US1543569A - Aminoalkylaminonaphthalene sulphonic acids - Google Patents
Aminoalkylaminonaphthalene sulphonic acids Download PDFInfo
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- US1543569A US1543569A US13610A US1361025A US1543569A US 1543569 A US1543569 A US 1543569A US 13610 A US13610 A US 13610A US 1361025 A US1361025 A US 1361025A US 1543569 A US1543569 A US 1543569A
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- acid
- sulphonic acids
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- 239000002253 acid Substances 0.000 title description 29
- 150000007513 acids Chemical class 0.000 title description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000000843 powder Substances 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 7
- -1 aliphatic diamines Chemical class 0.000 description 7
- 150000002832 nitroso derivatives Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 6
- RUFPHBVGCFYCNW-UHFFFAOYSA-N 1-naphthylamine Chemical compound C1=CC=C2C(N)=CC=CC2=C1 RUFPHBVGCFYCNW-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 229940012017 ethylenediamine Drugs 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 3
- 150000004985 diamines Chemical class 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 150000005002 naphthylamines Chemical class 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical compound OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- JBIJLHTVPXGSAM-UHFFFAOYSA-N 2-naphthylamine Chemical compound C1=CC=CC2=CC(N)=CC=C21 JBIJLHTVPXGSAM-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- GFNSFQFJOPXLSS-UHFFFAOYSA-N NCCC1=C(C2=CC(=CC=C2C=C1)S(=O)(=O)O)N Chemical compound NCCC1=C(C2=CC(=CC=C2C=C1)S(=O)(=O)O)N GFNSFQFJOPXLSS-UHFFFAOYSA-N 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000004780 naphthols Chemical class 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/28—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/45—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/47—Sulfonic acids having sulfo groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
Definitions
- Patented do 9 5250 UNITED STATES PATENT OFFICE.
- JOHANN HUISMANN OF WIESDORI, NEAR COLOGNE, WALTER DUISBERG, O1 LEVER- KUSEN, NEAR OOLOGNE, AND WINFRIED HENTRICH AND LUDWIG ZEH, O1 WIRE- DORF, NEAR COLOGNE, GERMANY, ASSIGNORS TO GRABSELLI nm'rurr COR PORATION, OF- NEW YORK, N. Y., A CORPORATION OF DELAWARE.
- aminonaphthalene Sulphonic Acids of which the following is a s cification.
- our invention resides in a process of producin o -aminoal l-substituted aminonapht alene sulphonic acids and in the compounds themselves, which are valuable dyestufi intermediates.
- naphthylamines areobtained. If aliphatic diamines such as ethylenediamine, or its homologues are allowed to react withthe naphthols both amino groups are liable to be substituted and mixtures of i. e. aminoethylamidonaphthalene, ethylenedinaphthylamines and eventually higher alkylated products are obtained.
- the mother liquor is practically free from raw material and from the desired end product.
- the separated product is sludged with water and boiled with h drochloric acid in order to expel all the sulp urous acid from the bisulfite.
- the aminoethyl-na hthionic acid scparatesand is filtered oil? It is a light greyish powder very diflicultly soluble even in hot water. I It forms a sodium salt which is soluble to a certain extent in hot water but also difiicultly soluble in cold water.
- Sus nded in water and treated with sodium nltrite and hydrochloric acid a nitroso ⁇ compound is quantitatively formed which nitroso compound is a crystalline yellowish colored powder relatively soluble in water.
- the sodium salt is slihtly soluble in hot water and very diflicifltly soluble in cold water.
- the nitroso compound is obtained by dissolving the sodium salt in hot water, adding the molecular equivalent of sodium nitrite and pouring the solution into ice cold diluted hydrochloric acid.
- the nitroso compound separates as beautiful orange colored crystals quite insoluble in cold water and soluble in hot water from which it can be re-crystallized.
- the 2- (aminoethyl) amino-8-naphthol-6-sulphonic acid is obtained with an excellent yield. It is a white powder diflicultly soluble in water but quite soluble in hot diluted hydrochloric acid. With nitrous acid it forms a brownish crystalline nitroso compound.
- Ewwmple 4.364 parts 2.8-dihydr0xynaphthalene-3.6-disulphonate of soda are suspended in 880 parts of a 40% sodium bisu to solution and 300 parts of a 20% aqueous solution of ethylenediamine and the mixture is-boiled at reflux for hours. The solution is then diluted with its volume of water and boiled with an excess of hydrochloric acid. After cooling the 2-(aminoethyl) -amino -8- hydroxynaphthalene-3.6-disulphonic acid is filtered ofl.
- Example 5.246 parts 2-naphth lamine- 7-sulphonate of soda are dissolv in 500 parts water and 880 arts of a 40% sodium isulfite solution ad ed. To this is added a solution of 241 parts normal butylenediamine-dichlorhydrate in 500 parts water and-.the mass heatedat -95 for about 16, hours. The o-amino-butylr2-naphthylamine-'Z-sul honic acid se arates as white floccules. r coolin e reaction product is filtered, the sulp onic acid dissolved in water and boiled with an excess of hydrochloric acid to .expel the sulfurous acid.
- the solution is then made slighltly alkaline by the addition of soda ash.
- e difiicultly soluble sodium salt of the m-aminobutyl-2- naphthylamine-7-sulphonate of soda separates is filtered oil and dried. It is a white powder easily soluble in dilute hydrochloric acid; with sodium nitrite in acld solution it forms a crystalline light yellow colored nitroso compound.
- the w-aminoalkylaminonaphthalene sulphonic acids which can be obtained by acting with ali hatic diamines in resence of soluble sa ts of sulfurous aci 5 upon naphthalene sulphonic acids having at least one of the reactive groups amino and hydroxyl, which maminoalkylamino naphthalene sulphonic acids are whitish powders generally diflicultly soluble in water, form alkali metal resence of souble salts of sulsalts, are soluble in dilute mineral acids and form characteristic, crystalline and colored nitroso compounds.
- m-aminoethylaminonaphthalene sulphonic acids which can be obtained by reacting with ethylene'diamine in presence of soluble salts of sulfurous acid upon naphthalene sulphonic acids having at least one of the reactive groups amino and hydroxyl, which m-aminoethylamino-naphthalene sulphonic acids are white powders, generally difiicultly soluble in water and orm alkali metal salts, soluble in dilute mineral acids and characteristic, colored-and c stalline nitroso compounds.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
26 or naphthylamines the corresponding a 55 form to -aminoalkyl u.
Patented do 9 5250 UNITED STATES PATENT OFFICE.
JOHANN HUISMANN, OF WIESDORI, NEAR COLOGNE, WALTER DUISBERG, O1 LEVER- KUSEN, NEAR OOLOGNE, AND WINFRIED HENTRICH AND LUDWIG ZEH, O1 WIRE- DORF, NEAR COLOGNE, GERMANY, ASSIGNORS TO GRABSELLI nm'rurr COR PORATION, OF- NEW YORK, N. Y., A CORPORATION OF DELAWARE.
AIINOALKYLAIINONAPHTHALENE SULPHONIC ACIDS.
1T0 Drawing.
To all whom it may concern:
Be it known that we, (1) JOHANN Hurs- MANN, (2) WALTER Dmsanne, (3) WI1 FRIED HENTRICH, and (4) LUDWIG Zen, citi- 5 sons of Germany, residing at (1) Wiesdorf,
aminonaphthalene Sulphonic Acids, of which the following is a s cification.
our invention resides in a process of producin o -aminoal l-substituted aminonapht alene sulphonic acids and in the compounds themselves, which are valuable dyestufi intermediates.
It is well known that by reacting with primary or secondar amines in presence of alkali metal bisu tes upon naphillglls In the foregoing formulae the sulphonic ral duction of our amino-alkylamino-na hthaacid group may occupy any of the save possible positions in the naphthalene nudone: as indicated. Both 1; of naphthalene sulphonic acids, that is, ose having the reactive roup in the alpha position and those having the reactive group in'the beta position react with aliphatic diamines m,
the same way, corresponding naphthol sulphonic acids and naphthylamine sulphonic acids giving the same end product.
In addition to the straight naphthol and naphthylamine sulphonic acids, aminonaph-l thol, dihydroxy-naphthaleneas well as naphthylene-diamin-sulphonic acids Application ma Iaroh a, 1925. Serial no. 1:,c1o.
naphthylamines areobtained. If aliphatic diamines such as ethylenediamine, or its homologues are allowed to react withthe naphthols both amino groups are liable to be substituted and mixtures of i. e. aminoethylamidonaphthalene, ethylenedinaphthylamines and eventually higher alkylated products are obtained.
We have now found that if aliphatic diamines are allowed to reactin presence of soluble salts of sulfurous acid upon naphthalene sulphonic. acids having one of the reactive groups, amino and h droxyl, only one of the amide groups is so tituted by a naphthalene nucleus, and m -aminoalkylaminonaphthalene sulphonic acids are obtained with excellent yields.
The reaction proceedsmost likely in the following way The diamines which we use for the prothe following examples in which the parts given are by weight Example 1.246 parts of lna hthol-4- sulphonate of soda are suspends in 880 parts of a sodium bisulfite solution to which 450 parts of a 20% aqueous solution of ethylene-diamine are added and the mixture is boiled at reflux with ood stirrin The naphthol sulphonic acid issolves grad ually. At the same time the 1- (aminoet yl)- amino-naphthalene-4-sulphonic acid se arates. The reaction is carried out at boiling temperature for several hours. The mixture is then cooled and filtered, on a vacuum filter. The mother liquor is practically free from raw material and from the desired end product. The separated product is sludged with water and boiled with h drochloric acid in order to expel all the sulp urous acid from the bisulfite. By cooling, the aminoethyl-na hthionic acid scparatesand is filtered oil? It is a light greyish powder very diflicultly soluble even in hot water. I It forms a sodium salt which is soluble to a certain extent in hot water but also difiicultly soluble in cold water. Sus nded in water and treated with sodium nltrite and hydrochloric acid a nitroso} compound is quantitatively formed which nitroso compound is a crystalline yellowish colored powder relatively soluble in water.
Exwmplc 2.246 parts of 2-naphthylamine-7-sulphonate of soda are suspended in 1750 parts of a 40% sodium bisulfite solution to which 900 parts of a 20% aqueous solution of eth lenediamine are added and the mixture is iled at reflux for 12hours .while stirring. The napthylamine sulphonic acid disolves gradually and then the 2 (aminoethyl) aminonaphthalene 7 sulphonic acid starts :to separate. After coolmg, the crystalline product is filtered ofi, sludged with hydrochloric acid to Congo acid reaction and boiled to expel the sulfurous acid. After cooling, the pure 2- (aminoethyl) -alminonaphthalene-7-sulphonic acid is filtered oil and dried. It is a white powder practically insoluble in cold and hot water,
the sodium salt is slihtly soluble in hot water and very diflicifltly soluble in cold water. The nitroso compound is obtained by dissolving the sodium salt in hot water, adding the molecular equivalent of sodium nitrite and pouring the solution into ice cold diluted hydrochloric acid. The nitroso compound separates as beautiful orange colored crystals quite insoluble in cold water and soluble in hot water from which it can be re-crystallized.
Exam Ze 3.-261 parts of 2-amido-8- naphtho -6-sulphona te of soda are suspended in. 1750 parts of a 40% sodium bisulfite solution to which 300 parts of a 20% aqueous solution of eth lenediamine are added. The mixture is bolled at reflux for 12 hours,
nuance cooled, filtered oil and the paste suspended in enough hydrochloric acid to secure Congo acid reaction at the end and, b boiling, all the sulfurous acid is expel ed. The 2- (aminoethyl) amino-8-naphthol-6-sulphonic acid is obtained with an excellent yield. It is a white powder diflicultly soluble in water but quite soluble in hot diluted hydrochloric acid. With nitrous acid it forms a brownish crystalline nitroso compound.
Ewwmple 4.364 parts 2.8-dihydr0xynaphthalene-3.6-disulphonate of soda are suspended in 880 parts of a 40% sodium bisu to solution and 300 parts of a 20% aqueous solution of ethylenediamine and the mixture is-boiled at reflux for hours. The solution is then diluted with its volume of water and boiled with an excess of hydrochloric acid. After cooling the 2-(aminoethyl) -amino -8- hydroxynaphthalene-3.6-disulphonic acid is filtered ofl. It contains traces of unconverted 2.8-dihydroxynaphthalene-3.6-disulphonic acid and ethylene- 2.2-diamino8.8 -dihydroxydinaphthy -3.3- 6.6'-tetrasulphonic acid. t is purified b recrystallization from hot water to whic sodium acetate has been added. It is a whitish powder easily soluble in hot water.
Example 5.246 parts 2-naphth lamine- 7-sulphonate of soda are dissolv in 500 parts water and 880 arts of a 40% sodium isulfite solution ad ed. To this is added a solution of 241 parts normal butylenediamine-dichlorhydrate in 500 parts water and-.the mass heatedat -95 for about 16, hours. The o-amino-butylr2-naphthylamine-'Z-sul honic acid se arates as white floccules. r coolin e reaction product is filtered, the sulp onic acid dissolved in water and boiled with an excess of hydrochloric acid to .expel the sulfurous acid.
The solution is then made slighltly alkaline by the addition of soda ash. e difiicultly soluble sodium salt of the m-aminobutyl-2- naphthylamine-7-sulphonate of soda separates is filtered oil and dried. It is a white powder easily soluble in dilute hydrochloric acid; with sodium nitrite in acld solution it forms a crystalline light yellow colored nitroso compound.
We claim '1. The process of producing m-aminoalkylamino-naphthalene sulphomc acids which consists in reacting wit aliphatic diamines in (presence of soluble salts of sulfurous aci upon naphthalene sulphonic acids having at least one of the reactive groups amino and hydro l.
2. The processo producing m-aminoalkylamino-naphthalene sulphonlc acids which consists in reacting in presence of soluble salts of sulfurous acid with ali haticdiamines upon naphthylamine sulp onic acids.
=3. The process of producing co-aminoethylamino-naphthalene sulphomc acids which III nuance consists in reactin with eth lene-diamine in presence of solub e salts 0 sulfurous acid upon naphthalene sulphonic acids having at least one of the reactive groups amino and h droxyl.
4. e process of producing m-aminoeLhylamino-naphthalene sulphonic acids, which consists in reactin with ethylenediamine in furous aci upon naphthylamine sulphonic acids. v
5. As new products the w-aminoalkylaminonaphthalene sulphonic acids which can be obtained by acting with ali hatic diamines in resence of soluble sa ts of sulfurous aci 5 upon naphthalene sulphonic acids having at least one of the reactive groups amino and hydroxyl, which maminoalkylamino naphthalene sulphonic acids are whitish powders generally diflicultly soluble in water, form alkali metal resence of souble salts of sulsalts, are soluble in dilute mineral acids and form characteristic, crystalline and colored nitroso compounds.
' 6. As new products the m-aminoethylaminonaphthalene sulphonic acids which can be obtained by reacting with ethylene'diamine in presence of soluble salts of sulfurous acid upon naphthalene sulphonic acids having at least one of the reactive groups amino and hydroxyl, which m-aminoethylamino-naphthalene sulphonic acids are white powders, generally difiicultly soluble in water and orm alkali metal salts, soluble in dilute mineral acids and characteristic, colored-and c stalline nitroso compounds.
11 testimony whereof we have hereunto set our hands.
J OHANITHUISMANN. WALTER DUISBERG. WINFRIED HENTRICH. LUDWIG ZEH.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13610A US1543569A (en) | 1925-03-06 | 1925-03-06 | Aminoalkylaminonaphthalene sulphonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US13610A US1543569A (en) | 1925-03-06 | 1925-03-06 | Aminoalkylaminonaphthalene sulphonic acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US1543569A true US1543569A (en) | 1925-06-23 |
Family
ID=21760823
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US13610A Expired - Lifetime US1543569A (en) | 1925-03-06 | 1925-03-06 | Aminoalkylaminonaphthalene sulphonic acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US1543569A (en) |
-
1925
- 1925-03-06 US US13610A patent/US1543569A/en not_active Expired - Lifetime
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